Hydrochloric Acid → 3-(benzyloxy)-5-(methylsulfinyl)-N-(4-methylthiazol-2-yl)pyridin-2-amine hydrochloride

HRID 1426092Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1426092
[CH2:1]([O:8][C:9]1[C:10]([NH:17][C:18]2[S:19][CH:20]=[C:21]([CH3:23])[N:22]=2)=[N:11][CH:12]=[C:13]([S:15][CH3:16])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C=C([Cl:30])C=C(C(OO)=[O:32])C=1.Cl>C(Cl)Cl.CCOCC>[ClH:30].[CH2:1]([O:8][C:9]1[C:10]([NH:17][C:18]2[S:19][CH:20]=[C:21]([CH3:23])[N:22]=2)=[N:11][CH:12]=[C:13]([S:15]([CH3:16])=[O:32])[CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 70297m-Chloroperbenzoic acidHCID 592256943-(benzyloxy)-N-(4-methylthiazol-2-yl)-5-(methylthio)pyridin-2-amine

Produkt 1

HCID 866396513-(benzyloxy)-5-(methylsulfinyl)-N-(4-methylthiazol-2-yl)pyridin-2-amine hydrochlorideAusbeute 56,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

3-(Benzyloxy)-N-(4-methylthiazol-2-yl)-5-(methylthio)pyridin-2-amine (prepared according to Example 7; 0.057 g, 0.166 mmol) was placed in CH2Cl2 (5 mL) and cooled to 0° C. MCPBA (0.0398 g, 0.166 mmol) was added, and the reaction mixture was stirred at room temperature for 2 hours, then quenched with sodium bisulfite and extracted with CH2Cl2. The organic layer was washed with saturated sodium bicarbonate, dried, filtered, and concentrated. The residue was purified by silica gel (40-80% EtOAc in hexanes) to give the free base. The free base was dissolved in CH2Cl2, and 2M HCl in ether was added. The solution was concentrated to give 3-(benzyloxy)-5-(methylsulfinyl)-N-(4-methylthiazol-2-yl)pyridin-2-amine hydrochloride (0.037 g, 56.3% yield). 1H NMR (DMSO-d6) δ 8.18 (d, 1H), 7.81 (d, 1H), 7.62 (m, 2H), 7.43 (m, 2H), 7.37 (m, 1H), 6.83 (s, 1H), 5.39 (d, 2H), 2.82 (s, 3H), 2.30 (s, 3H). Mass spectrum (apci) m/z=360.0 (M+H-HCl).

Aufarbeitung

  1. customquenched with sodium bisulfite
  2. extractionextracted with CH2Cl2
  3. washThe organic layer was washed with saturated sodium bicarbonate
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel (40-80% EtOAc in hexanes)
  8. customto give the free base
  9. concentrationThe solution was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-396e6b12d9194b7a834f7db2d62e9124
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08933077B2

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